Unusual phase transfer mechanism of the ruthenium-catalyzed oxidation of alcohols with hydrogen peroxide

被引:21
|
作者
Rothenberg, G [1 ]
Barak, G [1 ]
Sasson, Y [1 ]
机构
[1] Hebrew Univ Jerusalem, Casali Inst Appl Chem, IL-91904 Jerusalem, Israel
关键词
D O I
10.1016/S0040-4020(99)00206-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A kinetic investigation of the Ru-catalyzed oxidation of I-phenyl ethanol to acetophenone using KO, under PT conditions shows that this system differs from classic extraction and interfacial mechanisms often encountered in PTC oxidations. Vesicles formed by the phase transfer agent in the organic phase are proposed as the catalytic reaction sites. Such structures are evidenced by microscopic studies. The effects of substituents, different phase transfer agents, and metal catalysts are studied and discussed in view of this mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6301 / 6310
页数:10
相关论文
共 50 条
  • [1] Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism
    Sueki, Shunsuke
    Matsuyama, Mizuki
    Watanabe, Azumi
    Kanemaki, Arata
    Katakawa, Kazuaki
    Anada, Masahiro
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (31) : 4878 - 4885
  • [2] Ruthenium-catalyzed oxidation of alkenes, alkynes, and alcohols to organic acids with aqueous hydrogen peroxide
    Che, Chi-Ming
    Yip, Wing-Ping
    Yu, Wing-Yiu
    CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (03) : 453 - 458
  • [3] RUTHENIUM-CATALYZED OXIDATION OF PHENOLS WITH HYDROGEN-PEROXIDE
    ITO, S
    AIHARA, K
    MATSUMOTO, M
    TETRAHEDRON LETTERS, 1983, 24 (47) : 5249 - 5252
  • [4] RUTHENIUM-CATALYZED OXIDATION OF ALCOHOLS WITH PERACIDS
    MURAHASHI, SI
    NAOTA, T
    ODA, Y
    HIRAI, N
    SYNLETT, 1995, (07) : 733 - 734
  • [5] RUTHENIUM-CATALYZED OXIDATION OF ALCOHOLS BY ACETONE
    WANG, GZ
    BACKVALL, JE
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) : 337 - 339
  • [6] Ruthenium-Catalyzed Oxidation of Alcohols into Amides
    Watson, Andrew J. A.
    Maxwell, Aoife C.
    Williams, Jonathan M. J.
    ORGANIC LETTERS, 2009, 11 (12) : 2667 - 2670
  • [7] RUTHENIUM-CATALYZED OXIDATION OF PRIMARY ALCOHOLS WITH THE NEW OXIDATION SYSTEM N-METHYLMORPHOLINE/HYDROGEN-PEROXIDE
    BEHR, A
    EUSTERWIEMANN, K
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 403 (1-2) : 215 - 219
  • [8] An unusual ruthenium-catalyzed dimerization of propargyl alcohols
    Trost, BM
    Rudd, MT
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (36) : 8862 - 8863
  • [9] Ruthenium-Catalyzed Oxidation of Allyl Alcohols with Intermolecular Hydrogen Transfer: Synthesis of α,β-Unsaturated Carbonyl Compounds
    Ren, Kai
    Hu, Bei
    Zhao, Mengmeng
    Tu, Yahui
    Xie, Xiaomin
    Zhang, Zhaoguo
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (05): : 2170 - 2177
  • [10] RUTHENIUM-CATALYZED PARTIAL OXIDATION OF ALCOHOLS BY PARAFORMALDEHYDE
    NAM, JH
    KWON, JH
    YANG, SB
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1994, 15 (08) : 692 - 694